In this episode of Thoughts on Selling, I sit down with Jake Isham — filmmaker, creative director, and founder of Creative Minds Agency.

Jake’s story is pure art-meets-entrepreneurship. He started as an actor, moved behind the camera to direct, and somewhere along the way became what he calls an “accidental marketer.”

We dig deep into the intersection of storytelling, sales, and authenticity — how great art and great selling share the same purpose: to create an effect. Jake explains how the best salespeople are actually performers — not in a fake way, but in the sense that they listen, adapt, and stay present in the scene.

Our conversation bounces between filmmaking, improv, and enterprise sales, but it all comes back to one central idea: sales is an art form. The goal isn’t to pitch harder or talk faster; it’s to create a feeling that sticks.

A few big takeaways:

• 🎭 Sales and acting share the same core skill — presence. Great sellers listen, improvise, and respond in the moment.

• 💬 Be interested, not interesting. Shift the spotlight to the customer; that’s where trust begins.

• 🧠 Reps build mastery. Like athletes and artists, salespeople get better through repetition and reflection — not theory.

• 🔥 Authenticity beats polish. When you lead with genuine curiosity and passion, selling stops feeling like selling.

• 🎥 Personal brand is leverage. Jake shows how documenting your story builds trust and visibility that lasts beyond any one deal.

• 💡 The right views matter more than viral views. You don’t need a million followers — you need the right audience.

• Jake and I also talk about the business of creativity — how he learned to blend craft with commerce, the value of expertise (“knowing where to tap”), and why every creator, seller, and leader needs to believe in what they’re offering.

  It’s a fun, high-energy conversation about where art meets revenue — and how showing up as yourself is the real competitive edge.

  🎧 Give it a listen, and let me know what lands with you.

  #SalesLeadership #PersonalBranding #AuthenticSelling #Storytelling #ThoughtsOnSelling

In this episode of Thoughts on Selling, I sit down with Laura Keith, CEO of Hive Perform and Hive Learning — and self-proclaimed “Chief Entertainment Officer” of three kids. We dig into the psychology of selling, the human side of enablement, and how data, AI, and coaching are reshaping modern sales.

Laura’s journey from studying psychology to leading sales organizations is fascinating. She never planned to work in sales — but curiosity, empathy, and a deep understanding of human behavior naturally pulled her in. Those same traits now shape her leadership and the products she’s building at Hive Perform.

We talk about how sales has lost touch with its human side — too often focused on product features and process over people — and how AI might actually help bring humanity back into selling. As automation handles more of the science, the art becomes more valuable: listening deeply, reading motivation, and understanding buyer psychology.

A few big takeaways from our conversation:

• Sales is psychology. Understanding what makes buyers tick — their motivations, fears, and goals — is at the heart of effective selling.

• AI can’t replace empathy. The best sales reps will use AI as a tool but rely on human insight and curiosity to create connection.

• Coaching and practice drive performance. The highest-performing teams make time to practice and coach — not just inspect pipelines.

• Leaders must define “what good looks like.” Without clear frameworks, coaching and development can’t happen effectively.

• Data makes conversations objective. When performance data is visible, reps and leaders can focus on solving problems together, not defending opinions.

• Curiosity beats scripts. Great sellers ask one more question instead of firing back with a pre-rehearsed answer.

We wrap by talking about the future of sales enablement — one where data, AI, and human insight combine to make teams more adaptable, empathetic, and effective.

🎧 Give it a listen — and let me know what resonates most with you.

#SalesEnablement #SalesLeadership #AIinSales #PsychologyofSelling #ThoughtsOnSelling

In this episode of Thoughts on Selling, I sit down with Jeff Kirchick — sales leader, author, and big believer in authenticity. We dig into how authenticity plays out in sales, what AI can and can’t replace, and why building trust matters more than ever.

Jeff shares his journey from English major and aspiring screenwriter to startup sales leader, selling seven-figure deals to Fortune 500s. We talk about his book, the hard truths he learned writing it, and why he believes authenticity is the ultimate differentiator in a world where AI can generate scripts, emails, and playbooks.

We get into some fun and unexpected territory too — from Dennis Rodman and Larry David as surprising role models for authenticity, to the cultural differences between selling in Boston, Japan, and Boulder. The through-line? Real relationships, built on curiosity, honesty, and non-attachment to outcomes, are what drive sustainable success in sales.

A few key takeaways:

• Authenticity builds trust. Buyers can tell when you’re real — and they reward it.

• AI can’t replace relationships. Tools help, but risk management and shared experience still come from humans.

• Deliberate practice matters. Salespeople need to rehearse pivots and build confidence outside scripts.

• Non-attachment to outcomes frees you. Curiosity and care create openings, even if they don’t lead to immediate deals.

• Great leaders go first. Vulnerability and empathy from the top invite teams to bring their full selves.

This conversation is packed with stories, insights, and practical wisdom for anyone looking to level up as a sales leader or seller.

🎧 Give it a listen, and let me know what lands with you.

In this episode of Thoughts on Selling, I sit down with David Donlan, VP of Sales at IP Co-Pilot, longtime tech sales leader, and passionate mentor for the next generation of sales professionals.

David and I cover a wide range of topics — from his early days upselling azaleas with fertilizer at age 15 to shaping sales teams at HubSpot, and now building a company that helps innovators protect and accelerate patents.

A few highlights from our conversation:

• Three ways to sell. David breaks down selling on product (easy but competitive), outcomes (about solving real business problems), and feelings (the hardest, but most powerful when done well).

• The heart of leadership. Why helping SDRs and junior salespeople grow into leaders is one of the most rewarding parts of a career.

• Hiring with discipline. Scorecards, structured onboarding, and clear expectations turn hiring from a gamble into a repeatable, measurable process.

• Culture in action. It’s not about slogans on the wall; it’s about building a place where individual motivations are recognized and supported.

• From landscaping to leadership. How lessons from selling plants, teaching swim lessons, and working in services carried forward into leading tech sales organizations.

David also shares his excitement about IP Co-Pilot — and how reducing the patent process from years to weeks can completely change the trajectory of companies large and small.

This one’s packed with stories, lessons, and practical ideas you can put into play immediately.

🎧 Tune in — and let me know which part resonates most with your sales journey.

#SalesLeadership #SalesEnablement #TeamBuilding #ThoughtsOnSelling

In this episode of Thoughts on Selling, I sit down with Ted McKenna — researcher, author, and co-creator of some of the most influential sales frameworks of the past two decades. Ted has been behind The Challenger Sale, The JOLT Effect, and most recently, The Activator Advantage.

We dive into the evolving dynamics of B2B sales, why buyers are more informed (and more hesitant) than ever, and what high-performing sellers do differently.

Some highlights from our discussion:

• Data meets sales anthropology. Ted shares how deep analysis of 2.5 million sales calls revealed why more deals end in “no decision” — and what sellers can do about it.

• The JOLT Effect in practice. Why too much information overwhelms buyers, and how great sellers guide decisions rather than flood inboxes with decks.

• The Activator Advantage. A deep look at what makes “activators” so successful — consistent business development, building zipper relationships, and flowing value across networks.

• Fear of messing up. Discounts don’t move deals — risk and career impact do. Sellers must address the emotional side of decision-making.

• Authenticity wins. Buyers can spot when you’re coin-operated. The best sellers genuinely care about client outcomes and align their work with customer missions.

We also touch on AI’s role in selling, improv as sales training, and the timeless truth that how you sell matters more than what you sell.

🎧 This is one you’ll want to play back with your team.

#salesenablement #jolteffect #activatoradvantage #salescoaching #thoughtsonselling

In this episode of Thoughts on Selling, I sit down with AI strategist and workforce transformation expert Ben Tasker. Ben has spent over a decade helping organizations harness AI not just as a shiny tool, but as a way to amplify human abilities through upskilling, reskilling, and smarter systems thinking.

We dive into:

• The “AI Between Times”: why we’re in a transition period where adoption is fast, mistakes will happen, and systems thinking is essential.

• Upskilling & Reskilling: how organizations can build learning plans to keep talent relevant and amplify what people already do well.

• Applied AI in Sales: from RFP prep to simulated buyer conversations, how sales teams can use AI for deliberate practice and better customer engagement.

• Systems Thinking & Change Management: why AI adoption fails without clear processes, data quality, and organizational alignment.

• Personal Branding in the AI Era: how individuals can leverage AI to publish, create, and stay visible in a world where recommendation engines drive discovery.

Ben makes a strong case: While AI won’t replace us— those who embrace it will win over those who don’t.

If you’re a sales leader, enablement pro, or individual contributor wondering how to stay relevant in this exponential era of change, this conversation is for you.

👉 Connect with Ben at bentaskerai.com

In this episode of Thoughts on Selling, I sit down with Mike Baron — longtime sales leader, mentor, and operator who has lived the startup, PE, and enterprise trenches. Our conversation is part playbook, part reality check, and packed with practical wisdom for anyone leading or enabling sales teams.

We dive right into a “what if” scenario: if Mike were CRO and I were head of sales enablement at a security startup, what would we do first? Mike breaks it down with clarity:

• Start with comp plans. Keep them simple, transparent, and behavior-driving. A clear plan motivates, while a 65-page manual kills performance.

• Talk to customers — and closed-lost deals. Understand where you win, where you lose, and why. The gold is in the feedback loop.

• Assess the tech stack. Too many tools = administrivia. Too few = inefficiency. The goal: help reps spend more time selling.

From there, we cover the importance of defining an ICP that’s not just a “total addressable market” (because “anyone between 200 and 2,500 employees” isn’t a strategy). We talk about how to apply the “hive mind” to big deals by letting reps present stuck opportunities for group problem-solving.

We also dig into value selling: moving past feature talk to true business outcomes — revenue growth, OPEX reduction, market expansion. Mike shares how coaching, role play, and peer-led conversations shift reps into those business-focused dialogues.

A few key takeaways:

• Comp drives behavior. A well-built plan aligns sellers, customers, and company goals.

• Feedback is fuel. Win/loss analysis and customer conversations sharpen the value prop.

• Simplify to amplify. Tech should serve sellers, not bury them.

• Deliberate practice matters. Just like athletes, reps need repetition and coaching to build muscle memory.

• Celebrate the whole team. SEs, rev ops, legal — reward them too, not just quota carriers.

This is a fun, wide-ranging conversation full of actionable ideas. If you’re leading a team, building enablement, or just want to sharpen your own selling, you’ll take something useful away.

🎧 Tune in — and let me know what resonates most.

#salesleadership #salesenablement #valueselling #thoughtsonselling

In this episode, I sit down with Matt Wilkinson — life sciences marketer turned AI strategy partner, Visiting Fellow at Cranfield School of Management, and board member at the Association of Key Account Management. Matt brings a sharp lens to the challenges of sales and marketing alignment, the rise of AI in B2B, and what it really takes to create customers in today’s environment.

We cover a wide range of topics, from why account-based approaches are so powerful when done right, to how culture inside organizations shapes buying behavior, to the shifting role of brand and trust in an AI-driven world.

Some key takeaways from our conversation:

• Sales + Marketing must share the same North Star. Vanity metrics and siloed KPIs create friction instead of customers.

• Account-based strategy works best when sales and marketing co-create it. Alignment starts with shared target accounts, shared narratives, and shared wins.

• AI is rewriting the buying journey. Buyers come to conversations armed with custom, AI-generated insights — which means sellers need a point of view, not just information.

• Brand still matters. Even in a digital-first, bot-enabled world, strong brands reduce perceived risk and influence decisions.

• Know your customer deeply. Visit them, learn their culture, and align your story to their mission — whether that’s patient outcomes, revenue growth, or reducing risk.

• Trust and human connection win. Efficiency is not effectiveness; one meaningful, risk-reducing conversation beats 10,000 shallow ones.

Matt’s blend of academic insight, practical experience, and stories (yes, even about coffee makers!) makes this a conversation packed with perspective for anyone navigating modern B2B sales and marketing.

🎧 Give it a listen — and let me know what resonates with you.

#sales #marketing #AI #accountbasedmarketing #thoughtsonselling